The microbial oxidation of aromatic hydrocarbons to corresponding homochiral cyclohexadiene diols with mutant strains of Pseudomonas putida, discovered in the late 1960's by Gibson (Gibson, D. T., Hensley M., Yoshika H., Mabry, R. J., Biochemistry 9:1626 (1970)), opened new horizons in syntheses of chiral oxygenated compounds (see for example U.S. patent application Ser. No. 07/974,057, which is incorporated herein by reference). The utility of these chiral oxygenated compounds, which are versatile synthons, is reinforced by their use in enantiocontrolled syntheses as evidenced by several recent reviews. (Brown, M.S., "Organic Synthesis: Theory and Practice" (Hudlicky, T., Ed.), Vol. 2, 113, JAI Press, Greenwich, Conn. (1993); Carless, H. A. J., Tetrahedron: Asymmetry 3:795 (1992); Widdowson, D. A., Ribbons, D. W., Thomas, S. D., Janssen Chimica Acta 8:3 (1990)).
In the carbohydrate field the use of these chiral oxygenated synthons has recently been demonstrated in the preparation of cyclitols (see U.S. patent application Ser. No. 802,783, incorporated herein by reference), as well as four and five membered sugars such as protected L-erythrose 1 and its enantiomer (see U.S. Pat. No. 5,200,516 incorporated herein by reference), protected L-erythrolactone 2 (Hudlicky, T., Luna, H., Price, J. D., Rulin F., Tetrahedron Lett. 30:4053 (1989) and protected L-ribonic .gamma.-lactone 3 (Hudlicky, T., Price J. D., Synlett 159 (1990)). 2,3-O-Isopropylidene-L-erythruronolactone 4 is a versatile chiral synthon that has been used in many enantioselective syntheses including the preparation of compounds 1, 2, and 3 shown below and (-)-trihydroxyheliotridane 5 (Hudlicky, T., Luna, H., Price, J. D., Rulin, F., J. Org. Chem. 55:4683 (1990); and enone 6 (Hudlicky, T., Natchus, M. G., Nugent, T. C., Synth. Commun. 22: 151 ( 1992 ) used in the synthesis of PGE.sub.2.alpha. (Hudlicky, T., Luna, H., Barbieri, G., Kwart, L. D., J. Am. Chem. Soc. 110:4735 (1988); Johnson, C. R., Penning, T. D., J. Am. Chem. Soc. 108:5655 (1986)) and specionin (Hudlicky, T., Natchus, G. M., J. Org. Chem. 57:4740 (1992)). Recently, compound 4 appeared to be of particular interest as the key intermediate in the synthesis of dipeptide renin inhibitor, dihydroxyethylene isostere (Baker, W. R., Condon, S. L., Tetrahedron Lett. 33:1581 (1992) 7. ##STR1##
Known methods for the preparation of 4 include syntheses starting from ribonolactone (Beer, D., Meuwly, R., Vasella, A., Helv. Chim. Acta 65:2570 (1982)), chlorobenzene (Hudlicky, T., Luna, H., Price, J. D., Rulin, F., Tetrahedron Lett. 30:4053 (1989); Hudlicky, T., Luna, H., Price, J. D., Rulin, F., J. Org. Chem. 55:4683 (1990)) and D-gulonolactone (Borchardt, R. T., Wolfe, M. S., Anderson, B. L., Borcherding, D. R., J. Org. Chem. 55:4712 (1990); Borchardt, R. T., Borcherding, D. R., Scholtz, S. A., J. Org. Chem. 52:5457 (1987)) (cyclohexylidene protection group)); however, many of these routes are problematic in that they comprise multiple steps, are not scaleable to commercial levels or use environmentally undesirable reagents or conditions. The procedure of the present invention appears to be effective in both cost and the use of environmentally acceptable protocol and, therefore, is a desirable improvement over that known in the art.